Journal
ACS OMEGA
Volume 7, Issue 14, Pages 12015-12020Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.2c00214
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DKP formation is a common side reaction in solid-phase peptide synthesis, especially in the Fmoc-deprotection step. Secondary amino acids are more prone to this reaction. Using 2% DBU/5% piperazine/NMP instead of 20% piperidine/DMF significantly reduces DKP formation.
DKP (diketopiperazine) formation is a ubiquitous side reaction in SPPS (solid-phase peptide synthesis) that is highly sequence-dependent. Secondary amino acids are extremely prone to host such a side reaction. DKP formation is predominantly induced at the Fmoc (fluorenylmethyloxycarbonyl)-removal step mediated by a secondary amine, which conventionally employs piperidine/DMF (dimethylformamide). In this study, alternative Fmoc-removal solution 2% DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)/5% piperazine/NMP (N-methyl-2-pyrrolidone) led to drastic DKP reduction relative to 20% piperidine/DMF.
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